Yazar "Yakan, Hasan" seçeneğine göre listele
Listeleniyor 1 - 12 / 12
Sayfa Başına Sonuç
Sıralama seçenekleri
Öğe Experimental and theoretical investigations on a furan-2-carboxamide-bearing thiazole: synthesis, molecular characterization by IR/NMR/XRD, electronic characterization by DFT, Hirshfeld surface analysis and biological activity(Int Union Crystallography, 2022) Cakmak, Sukriye; Kirca, Basak Kosar; Veyisoglu, Aysel; Yakan, Hasan; Ersanli, Cem Cuneyt; Kutuk, HalilA thiazole-based heterocyclic amide, namely, N-(thiazol-2-yl)furan-2-carbox-amide, C8H6N2O2S, was synthesized and investigated for its antimicrobial activity. The structure was characterized by elemental analysis and IR, H-1 NMR, and C-13 NMR spectroscopy. The molecular and electronic structures were investigated experimentally by single-crystal X-ray diffraction (XRD) and theoretically by density functional theory (DFT) modelling. The compound crystallized in the monoclinic space group P2(1)/n and the asymmetric unit contains two symmetrically independent molecules. Several noncovalent interactions were recorded by XRD and analysed with Hirshfeld surface analysis (HSA) calculations. Natural bond orbital, molecular electrostatic potential, second-order nonlinear optical and thermodynamic property analyses were also carried out using the DFT/B3LYP method. The title compound was evaluated for antimicrobial activity against eight microorganisms consisting of Gram-negative bacteria, Gram-positive bacteria and fungi. The compound showed good antimicrobial activity against the eight tested microorganisms. This suggests that the compound merits further study for potential pharmacological and medical applications.Öğe Inhibitory effects of sulfenimides on human and bovine carbonic anhydrase enzymes(Taylor & Francis Ltd, 2023) Yakan, Hasan; Bilir, Gurkan; Cakmak, Sukriye; Tas, Omer; Karakullukcu, Nalan Turkoz; Soydan, Ercan; Kutuk, HalilA series of sulfenimide derivatives (1a-i) were investigated as inhibitors of human (hCA-I, hCA-II) and bovine (bCA) carbonic anhydrase enzymes. The compounds were synthesised by the reaction of substituted thiophenols with phthalimide by means of an effective, simple and eco-friendly method and the structures were confirmed by IR, H-1 NMR, C-13 NMR, MS and elemental analysis. All derivatives except for the methyl derivative (1b) exhibited effective inhibitory action at low micromolar concentrations on human isoforms, but only four derivatives (1e, 1f, 1h, 1i) inhibited the bovine enzyme. The bromo derivative (1f) was found to be strongest inhibitor of all three enzymes with KI values of 0.023, 0.044 and 20.57 mu M for hCA-I, hCA-II and bCA, respectively. Results of our study will make valuable contributions to carbonic anhydrase inhibition studies for further investigations since inhibitors of this enzyme are important molecules for medicinal chemistry.Öğe New 5-methylisatin including thiocarbohydrazones: preparation, structure elucidation and antimicrobial activity(Springer, 2022) Yakan, Hasan; Cakmak, Sukriye; Buruk, Osman; Veyisoglu, Aysel; Muglu, Halit; Karakullukcu, Nalan TurkozNew 5-methylisatin including thiocarbohydrazones (1-5) have been synthesized. The chemical structure of synthesized compounds was elucidated with IR, H-1 NMR, C-13 NMR spectroscopic methods, and elemental analysis. Moreover, the synthesized compounds have been screened for antimicrobial activity. Their antibacterial activities were tested against Gram-positive (Bacillus subtilis ATCC 6623, Staphylococcus aureus ATCC 25923, Enterococcus faecalis ATCC 29212), Gram-negative (Escherichia coli ATCC 25922, Klebsiella pneumoniae ATCC 70060, Pseudomonas aeruginosa ATCC 27853), and fungal (Candida albicans ATCC 10231, Aspergillus niger ATCC 16404) microbial strains using the microdilution method. In the isatin series, particularly the compound 2 showed the best antimicrobial activity against E. faecalis strain with MIC values of 64 mu g/mL compared to other compounds. This high activity of compound 2 is due to the presence of two electron-donating methoxy groups in its structure. The remaining substituted compounds have shown good and moderate antimicrobial activity compared to standard drugs. The results may provide insights into the target compounds' structure-activity relationships, which may facilitate the development of pharmacological and biological applications for the target compounds. Graphical abstract New isatins bearing thiocarbohydrazone were synthesized. Structures of all com- pounds were elucidated with spectroscopic approaches. The antimicrobial activities of the tested compounds presented promising antimicrobial activity against the eight tested microorganisms.Öğe Preparation, spectroscopic, X-ray crystallographic, DFT, antimicrobial and ADMET studies of N-[(4-flourophenyl)sulfanyl]phthalimide(Int Union Crystallography, 2023) Cakmak, Sukriye; Aycan, Tugba; Yakan, Hasan; Veyisoglu, Aysel; Tanak, Hasan; Evecen, MeryemN-[(4-Fluorophenyl)sulfanyl]phthalimide (C14H8FNO2S, FP) was synthesized and characterized using X-ray crystallography. It was then investigated via quantum chemical analysis using the density functional theory (DFT) approach, as well as spectrochemically using FT-IR and H-1 and C-13 NMR spectroscopy, and elemental analysis. The observed and stimulated spectra are in very good agreement for the DFT method. The in vitro antimicrobial activity of FP against three Gram-positive bacteria, three Gram-negative bacteria and two fungi were determined using the serial dilution method, and FP showed the highest anti-bacterial activity against E. coli, with a MIC of 128 mu g ml(-1). Druglikeness, ADME (absorption, distribution, metabolism and excretion) and toxicology studies were carried out to theoretically examine the drug properties of FP.Öğe Spectroscopic Properties and Preparation of Some 2,3-Dimethoxybenzamide Derivatives(Bentham Science Publ Ltd, 2016) Cakmak, Sukriye; Kutuk, Halil; Odabasoglu, Mustafa; Yakan, Hasan; Buyukgungor, OrhanIn this study, a series of substituted secondary amide compounds were synthesized starting from 2,3-dimethoxybenzoic acid and aniline derivatives. The structures of these synthesized compounds were determined using IR, H-1 NMR and C-13 NMR spectroscopy, X-ray diffraction and elemental analysis techniques. Background: Amides are important groups in organic compounds. Amides moieties are found in many natural products. We now report a complementary study of the amide derivatives and the structures of these synthesized compounds were determined using IR, H-1 NMR and C-13 NMR spectroscopy, X- ray diffraction and elemental analysis techniques. Methods: Substituted secondary amides were prepared from the corresponding 2,3-dimethoxybenzoic acid. This involved reaction of 2,3-dimethoxybenzoyl chloride with the appropriate aniline derivatives in the presence of THF to give substituted secondary amides. Results: A summary of crystallographic data, experimental details, and refinement results for compounds are given. Conclusion: In this study a simple, yet effective method was used for the synthesis of some benzamides from acyl chlorides with aniline and its derivatives in the presence of triethylamine. All the products were obtained with moderate-good yields.Öğe Synthesis of some symmetric disulfides from thiophthalimides and amines under microwave irradiation(World Research Association, 2018) Yakan, Hasan; Karakullukcu, Nalan Turkoz; Cakmak, Sukriye; Kutuk, HalilSome symmetric disulfides have been astonishingly prepared from thiophthalimides (sulfenimides) and amines in the presence of 2-ethoxyethanol (β-ee, neat) at microwave irradiation under free catalyst and ligand. The products were obtained in good to excellent yields ranging from 62% to 92%. When only thiophthalimides were exposed to microwave irradiation, disulfides were not obtained. Also, disulfides were not obtained from thiophthalimides in the presence of 2-ethoxyethanol (neat) under microwave irradiation. We compared the microwave-assisted synthesis method with the classical method. The products obtained were purified with chromatographic method and the analysis of them was performed with IR, 1H NMR, 13C NMR spectroscopic and elemental methods. © 2018 World Research Association. All rights reserved.Öğe Synthesis, characterization, antioxidant, and antibacterial activities of new 2,3-dimethoxy and 3-acetoxy-2-methyl benzamides(Springer, 2020) Yakan, Hasan; Cakmak, Sukriye; Kutuk, Halil; Yenigun, Semiha; Ozen, TevfikWe performed a series of novel benzamide compounds which were synthesized starting from 2,3-dimethoxybenzoic acid or 3-acetoxy-2-methylbenzoic acid and amine derivatives. All the obtained products were purified, and the analysis of these products was determined with IR, H-1 NMR, C-13 NMR spectroscopic, and elemental methods. The in vitro antioxidant activity of all the compounds was determined by total antioxidant, free radical scavenging, and metal chelating activity. Some of synthesized compounds showed more effective total antioxidant, free radical scavenging, and metal chelating activity compared with standards. One of the benzamide compounds has been shown to exhibit effective metal chelate activity. The new compounds were determined in vitro antibacterial activity against three gram-positive bacteria and three gram-negative bacteria and compared with two control drugs. Thus, by conducting in vivo biochemical tests of effective amides, researches can be carried out in different fields of application. Graphic abstract We performed a series of novel benzamide compounds which were synthesized, and the analysis of these products was determined with IR, H-1 NMR, C-13 NMR spectroscopic, and elemental methods. The in vitro antioxidant activity of all the compounds was determined by total antioxidant, free radical scavenging, and metal chelating activity. All the compounds were tested for their in vitro growth inhibitory activity against different bacteria.Öğe Synthesis, Spectroscopic Characterization, Single-Crystal Structure, Hirshfeld Surface Analysis, and Antimicrobial Studies of 3-Acetoxy-2-methylbenzoic Anhydride(Amer Chemical Soc, 2022) Cakmak, Sukriye; Kansiz, Sevgi; Azam, Mohammad; Veyisoglu, Aysel; Yakan, Hasan; Min, KimWe report a novel anhydride derivative, 3-acetoxy-2-methylbenzoic anhydride (AMA), obtained from the interaction of 3-acetoxy-2-methylbenzoyl chloride with 3-acetoxy-2-methylbenzoic acid. The synthesized compound was characterized by elemental analysis, IR, H-1 NMR, and C-13 NMR spectroscopic studies and single-crystal X-ray crystallography which revealed the crystallization of AMA as monoclinic with space group P2(1)/c. A Hirshfeld surface analysis was performed to record various intermolecular interactions, indicating the stabilization of the AMA structure by the intermolecular weak C-H center dot center dot center dot O hydrogen bonds and pi center dot center dot center dot pi interactions. The title compound was screened for antibacterial and antifungal activities using a serial dilution technique under aseptic conditions. The results indicate that the title compound has significant antibacterial properties but showed no antifungal behavior.Öğe Synthesis, Structural Investigation, Hirshfeld Surface Analysis, and Biological Evaluation of N-(3-Cyanothiophen-2-yl)-2-(thiophen-2yl)acetamide(Amer Chemical Soc, 2022) Cakmak, Sukriye; Kansiz, Sevgi; Azam, Mohammad; Ersanli, Cem Cuneyt; Idil, Onder; Veyisoglu, Aysel; Yakan, HasanIn this study, a novel heterocyclic amide derivative, N-(3-cyanothiophen- 2-yl)-2-(thiophen- 2-yl)acetamide (I), was obtained by reacting 2-aminothiophene-3-carbonitrile with activated 2-(thiophen-2-yl)acetic acid in a N-acylation reaction and characterized by elemental analyses, FT-IR, H-1 and C-13 NMR spectroscopic studies, and single crystal X-ray crystallography. The crystal packing of I is stabilized by C-H center dot center dot center dot N and N-H center dot center dot center dot N hydrogen bonds. In addition, I was investigated computationally using the density functional theory (DFT) method with the B3LYP exchange and correlation functions in conjunction with the 6311++G(d,p) basis set in the gas phase. Fukui function (FF) analysis was also carried out. Electrophilicity-based charge transfer (ECT) method and charge transfer (Delta N) were computed to examine the interactions between I and DNA bases (such as guanine, thymine, adenine, and cytosine). The most important contributions to the Hirshfeld surface are H center dot center dot center dot H (21%), C center dot center dot center dot H (20%), S center dot center dot center dot H (19%), N center dot center dot center dot H (14%), and O center dot center dot center dot H (12%). An ABTS antioxidant assay was used to evaluate the in vitro antioxidant activity of I. The compound exhibited moderate antioxidant activity. The antimicrobial activity of the title molecule was investigated under aseptic conditions, using the microdilution method, against Gram-positive and Gram-negative bacterial strains, and it also demonstrated significant activity against yeasts (Candida glabrata ATCC 90030, Candida krusei ATCC 34135). The findings revealed that the molecule possesses significant antioxidant and antimicrobial properties.Öğe Synthesis, structure elucidation, biological activity, enzyme inhibition and molecular docking studies of new Schiff bases based on 5-nitroisatin-thiocarbohydrazone(Elsevier, 2023) Yakan, Hasan; Omer, Hiba-H. S.; Buruk, Osman; Cakmak, Sukriye; Marah, Sarmad; Veyisoglu, Aysel; Muglu, HalitNew Schiff bases bearing 5-nitroisatin-thiocarbohydrazone ( 1-9 ) have been prepared. The chemical structures of these compounds have been clarified by spectroscopic methods (IR, 1 H NMR, and 13 C NMR), and elemental analysis. Besides, they have been tested for antimicrobial activity. The antimicrobial activities of the novel compounds have been evaluated using a twofold serial dilution method for Minimum Inhibitory Concentration (MIC) against three gram-positive bacteria, three gram-negative bacteria, and two fungal pathogens. The obtained data showed that compound 7 has excellent activity against gram-strain positive and gram-strain-negative bacteria. Compound 7 showed better activity than amoxicillin, which is one of the standard drugs used against the E. faecalis pathogen, but showed the same activity as tetracycline. Synthesized compounds could be formed the basis for the development of better antibacterial agents. The total antioxidant activity of compounds 3 and 5 showed better antioxidant activity than standard BHT, while compounds 4, 8, 7, 2 , and 6 showed better antioxidant activity than standard Trolox. The urease inhibitory effect of compound 7 was better than thiourea. Also, the structure-activity relationship study showed that the scores of molecular models revealed that the compounds with the highest number of binding with urease enzyme were compounds 3 and 7 with total bond numbers of 19 and 18, respectively.(c) 2022 Elsevier B.V. All rights reserved.Öğe Synthesis, X-ray structure, antimicrobial activity, DFT and molecular docking studies of N-(thiophen-2-ylmethyl)thiophene-2-carboxamide(Int Union Crystallography, 2022) Cakmak, Sukriye; Demircioglu, Zeynep; Uzun, Serap; Veyisoglu, Aysel; Yakan, Hasan; Ersanli, Cem CuneytIn the present study, N-(thiophen-2-ylmethyl)thiophene-2-carboxamide, C10H9-NOS2, (I), was obtained by the reaction of thiophene-2-carbonyl chloride and thiophen-2-ylmethanamine. Characterization of (I) was carried out using X-ray diffraction, spectroscopic techniques and elemental analyses. The DFT/B3LYP/ 6-311++G(d,p) theoretical level was successfully applied to calculate the optimized geometry and the local and global chemical activity parameters. The results obtained show good agreement between the experimental and theoretical geometrical parameters. The local and global chemical activity parameters were examined to determine the electrophilic and nucleophilic sites in (I). The natural bond orbital (NBO) analysis of (I) gives an efficient methodology for investigating the inter- and intramolecular bonding, as well as giving a convenient basis for investigating charge transfer or conjugative interactions in molecular systems. Also, the antimicrobial activity of (I) was investigated against eight microorganisms using the microdilution method and it is found to have an effective antibacterial activity. In addition, molecular docking studies were calculated in order to understand the nature of the binding of (I) with a lung cancer protein (PDB entry 1x2j).Öğe Two new benzamides: Synthesis, spectroscopic characterization, X-ray diffraction, and electronic structure analyses(Elsevier, 2020) Kirca, Basak Kosar; Cakmak, Sukriye; Yakan, Hasan; Odabasoglu, Mustafa; Buyukgungor, Orhan; Kutuk, HalilThis work includes the syntheses, molecular and electronic structure analyses of two novel secondary amide compounds 3-acetoxy-2-methyl-N-(2-methoxyphenyl)benzamide, 1 and 3-acetoxy-2-methyl-N-(3-methylphenyl)benzamide, 2. The title compounds were characterized by X-ray single crystal diffraction, FT-IR, H-1 NMR and (CNMR)-C-13-N- techniques and quantum chemical calculations were used for the investigations on electronic structure. X-ray diffraction analyses show that both compounds 1 and 2 crystallized in the triclinic system with space group P-1. While the characteristic amide bands were observed in IR and NMR spectra, crystallographic studies indicate that the supramolecular structures were stabilized by intramolecular and intermolecular hydrogen bonds and C-H center dot center dot center dot pi interactions for both compounds. Beside the experimental studies, natural bond orbital and molecular electrostatic potential analyses were carried out to understand the intramolecular charge transfers and hydrogen bonding behaviors of compounds. (C) 2019 Elsevier B.V. All rights reserved.
